Imidazole → Ethyl p-(1-imidazolylmethyl)cinnamate

HRID 903163Notes

Reaction equation

HRID 903163 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Na+].Br[CH2:9][C:10]1[CH:22]=[CH:21][C:13]([CH:14]=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=1>CN(C)C=O.[Ag].[N+]([O-])([O-])=O.[Ag+]>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:9][C:10]1[CH:22]=[CH:21][C:13]([CH:14]=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 795Imidazole2×HCID 14798Sodium HydroxideHCID 248203732-Propenoic acid, 3-[4-(bromomethyl)phenyl]-, ethyl ester

Product 1

HCID 70455277Ethyl p-(1-imidazolylmethyl)cinnamate

Reagents, catalysts & solvents 3

HCID 23954SilverCatalystHCID 24470Silver NitrateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 1.75 g of silver salt of imidazole, which was prepared from imidazole and silver nitrate in a sodium hydroxide solution, and 2.7 g of ethyl p-bromomethylcinnamate in 50 ml of N,N-dimethylformamide was heated at 100° C. for 7 hours.

Sources & evidence

ORD record
ord-00e0085f31a44ebb9e93f42425277db0
Source dataset
uspto-grants-1980_10
Patent number
US04226878

Reaction notes

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